Methanol → HCID 57634176, compound

Participants

Reaction Conditions

Reaction Steps

To (S)-3-(dibenzylamino)-4-(4-(trifluoromethyl)phenyl)butan-2-one (8.00 g, 19.4 mmol) in a 1 L round bottom flask was added MeOH (106 mL) and THF (35 mL). The mixture was cooled to −20° C. in a dry ice/acetone bath, and sodium borohydride (1.54 g, 40.8 mmol) was added. After 50 minutes, brine (200 mL) was added, and the mixture was extracted with ether (2×200 mL). The ether was washed with brine (50 mL), dried over sodium sulfate, and evaporated to provide an aqueous/oily mixture. The mixture was taken up in EtOAc (100 mL), washed with brine (50 mL), and the brine was back extracted with EtOAc (2×50 mL). The combined organic layers were dried over sodium sulfate and evaporated to a colorless oil. The oil was taken up in hexane and a white precipitate quickly formed. The precipitate was dissolved in hot hexane and left to stand at room temperature. Needles slowly formed, and the flask was cooled at −20° C. for 16 hours. The solid was recovered by filtration through a medium scintered glass funnel. The filtrate was evaporated and 1.4 g of colorless oil was recovered. The oil was dissolved in 6 mL hexane and cooled at −20° C. After 6 hours, the hexane was decanted and the white solid was placed under high vacuum. The two crops were combined to provide (2S,3S)-3-(dibenzylamino)-4-(4-(trifluoromethyl)phenyl)butan-2-ol (7.30 g, 90.8% yield) as a white crystalline solid. LCMS (ES+) m/z=414.3; 1H NMR (400 MHz, CDCl3) δ ppm 0.97 (d, J=6.06 Hz, 3H) 2.67-2.75 (m, 1H) 2.76-2.88 (m, 1H) 3.15 (dd, J=14.28, 5.67 Hz, 1H) 3.38 (d, J=13.30 Hz, 2H) 3.70-3.81 (m, 1H) 3.94 (d, J=13.30 Hz, 2H) 4.13 (s, 1H) 7.16-7.35 (m, 12H) 7.57 (d, J=7.83 Hz, 2H).

Provenance & Evidence